1-Bromo-4-fluorobenzene → HCID 19811580, compound

HRID 373102Notes

Reaction equation

HRID 373102 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[Mg].[CH2:10]([C:12]([CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([CH2:15][CH3:16])[CH:13]=[O:14])[CH3:11].[NH4+].[Cl-]>O1CCCC1>[CH2:10]([C:12]([CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([CH2:15][CH3:16])[CH:13]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:14])[CH3:11]

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19811581HCID 19811581, compound

Product 1

HCID 19811580HCID 19811580, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

20.4 g (0.116 mol) of 4-fluorobromobenzene in 250 ml of tetrahydrofuran are added dropwise to 2.8 g of magnesium turnings (0.166 mol) and stirring is carried out for half an hour at RT. 11 g (0.058 mol) of 2-ethyl-2-(pyrid-3-ylmethyl)-butanal in 100 ml of tetrahydrofuran are then slowly added dropwise. After 2 hours, the mixture is poured onto ice water and brought to pH 8 with saturated NH4Cl solution. It is extracted with ether, the organic phase is washed with water and dried over Na2SO4 and the solvent is then evaporated off. 8 g (48%) of the title compound are obtained as a viscous oil (compound No. 70 in the Table).

Workup

  1. waitis carried out for half an hour at RT
  2. additionthe mixture is poured onto ice water
  3. extractionIt is extracted with ether
  4. washthe organic phase is washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is then evaporated off

Sources & evidence

ORD record
ord-f6373133b1e642dbaa60779cfd9b06b5
Source dataset
uspto-grants-1992_11
Patent number
US05162329

Reaction notes

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